3'-Dephenyl-10-(N,N-dimethylcarbamoyl)-3'-(2-methyl-2-propenyl)docetaxel

ID: ALA339370

PubChem CID: 10724266

Max Phase: Preclinical

Molecular Formula: C44H60N2O15

Molecular Weight: 856.96

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)O[C@@]12CO[C@@H]1C[C@H](O)[C@@]1(C)C(=O)[C@H](OC(=O)N(C)C)C3=C(C)[C@@H](OC(=O)[C@H](O)[C@H](C=C(C)C)NC(=O)OC(C)(C)C)C[C@@](O)([C@@H](OC(=O)c4ccccc4)[C@H]21)C3(C)C

Standard InChI:  InChI=1S/C44H60N2O15/c1-22(2)18-26(45-38(53)61-40(5,6)7)31(49)37(52)57-27-20-44(55)35(59-36(51)25-16-14-13-15-17-25)33-42(10,28(48)19-29-43(33,21-56-29)60-24(4)47)34(50)32(58-39(54)46(11)12)30(23(27)3)41(44,8)9/h13-18,26-29,31-33,35,48-49,55H,19-21H2,1-12H3,(H,45,53)/t26-,27-,28-,29+,31+,32+,33-,35-,42+,43-,44+/m0/s1

Standard InChI Key:  MXWOSKYQGCYTDP-GNAFXECPSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA339370

   [(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-acetyloxy-12-(dimethylcarbamoyloxy)-1,9-dihydroxy-15-[(2R,3S)-2-hydroxy-5-methyl-3-[(2-methylpropan-2-yl)oxycarbonylamino]hex-4-enoyl]oxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 856.96

Molecular Weight (Monoisotopic): 856.3994

AlogP: 3.56

#Rotatable Bonds: 9

Polar Surface Area: 233.76

Molecular Species: NEUTRAL

HBA: 15

HBD: 4

#RO5 Violations: 2

HBA (Lipinski): 17

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 10.54

CX Basic pKa: ┄

CX LogP: 3.11

CX LogD: 3.11

Aromatic Rings: 1

Heavy Atoms: 61

QED Weighted: 0.16

Np Likeness Score: 1.89

References

1. Ojima I, Slater JC, Michaud E, Kuduk SD, Bounaud PY, Vrignaud P, Bissery MC, Veith JM, Pera P, Bernacki RJ..  (1996)  Syntheses and structure-activity relationships of the second-generation antitumor taxoids: exceptional activity against drug-resistant cancer cells.,  39  (20): [PMID:8831755] [10.1021/jm9604080]

2. Ojima I, Wang X, Jing Y, Wang C..  (2018)  Quest for Efficacious Next-Generation Taxoid Anticancer Agents and Their Tumor-Targeted Delivery.,  81  (3): [PMID:29468872] [10.1021/acs.jnatprod.7b01012]

Source

Source(1):

• Scientific Literature